1.
Pomegranate ellagitannin
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The pomegranate ellagitannins, which include punicalagin isomers, are ellagitannins found in the fruit, rind, bark or heartwood of pomegranates. As the chemistry of punicalagins became known it was found to be not unique to pomegranate, punicalagins are present in numerous species of the genus Terminalia, species chebula Retz. myriocarpa, catappa and citrina. They have also been isolated from Cistus salvifolius and Combretum molle, pomegranate fruits natural phenols can be extracted with ethyl acetate and fractionation can afford the ellagitannin punicalagins. A few dietary supplements and nutritional ingredients are available that contain extracts of whole pomegranate and/or are standardized to punicalagins, extracts of pomegranate are also Generally Recognized As Safe by the United States. Pedunculagin, a found in the pericarp of the pomegranate

2.
Phenols
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In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of a hydroxyl group bonded directly to an aromatic hydrocarbon group. The simplest of the class is phenol, which is also called carbolic acid C 6H 5OH, phenolic compounds are classified as simple phenols or polyphenols based on the number of phenol units in the molecule. Synonyms are arenols or aryl alcohols, phenolic compounds are synthesized industrially, they also are produced by plants and microorganisms, with variation between and within species. Although similar to alcohols, phenols have unique properties and are not classified as alcohols and they have higher acidities due to the aromatic rings tight coupling with the oxygen and a relatively loose bond between the oxygen and hydrogen. The acidity of the group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids. Phenols can have two or more hydroxy groups bonded to the ring in the same molecule. The simplest examples are the three benzenediols, each having two groups on a benzene ring. Organisms that synthesize phenolic compounds do so in response to pressures such as pathogen and insect attack, UV radiation. As they are present in food consumed in human diets and in used in traditional medicine of several cultures, their role in human health. Some phenols are germicidal and are used in formulating disinfectants, others possess estrogenic or endocrine disrupting activity. They can also be classified on the basis of their number of phenol groups and they can therefore be called simple phenols or monophenols, with only one phenolic group, or di-, tri- and oligophenols, with two, three or several phenolic groups respectively. The phenolic unit can be found dimerized or further polymerized, creating a new class of polyphenol, two natural phenols from two different categories, for instance a flavonoid and a lignan, can combine to form a hybrid class like the flavonolignans. Nomenclature of polymers, Plants in the genus Humulus and Cannabis produce terpenophenolic metabolites, phenolic lipids are long aliphatic chains bonded to a phenolic moiety. The majority of compounds are solubles molecules but the smaller molecules can be volatiles. Many natural phenols present chirality within their molecule, an example of such molecules is catechin. Cavicularin is an unusual macrocycle because it was the first compound isolated from nature displaying optical activity due to the presence of planar chirality, natural phenols chemically interact with many other substances. Stacking, a property of molecules with aromaticity, is seen occurring between phenolic molecules. When studied in mass spectrometry, phenols easily form adduct ions with halogens and they can also interact with the food matrices or with different forms of silica

3.
Gallic acid
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Gallic acid is a trihydroxybenzoic acid, a type of phenolic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. The chemical formula of gallic acid is C6H23COOH and it is found both free and as part of hydrolyzable tannins. The gallic acid groups are bonded to form dimers such as ellagic acid. Hydrolyzable tannins break down on hydrolysis to give gallic acid and glucose or ellagic acid and glucose, known as gallotannins and ellagitannins, gallic acid forms intermolecular esters such as digallic and trigallic acids, and cyclic ether-esters. Gallic acid can also be used as a material in the synthesis of the psychedelic alkaloid mescaline. The name is derived from oak galls, which were used to prepare tannic acid. Despite the name, gallic acid does not contain gallium, salts and esters of gallic acid are termed gallates. Pliny the Elder describes his experiments with it and writes that it was used to produce dyes, galls from oak trees were crushed and mixed with water, producing tannic acid. Gallic acid was one of the used by Angelo Mai, among other early investigators of palimpsests, to clear the top layer of text off. Mai was the first to employ it, but did so with a heavy hand, gallic acid was first studied by the Swedish chemist Carl Wilhelm Scheele in 1786. Gallic acid is a component of some pyrotechnic whistle mixtures, gallic acid is formed from 3-dehydroshikimate by the action of the enzyme shikimate dehydrogenase to produce 3, 5-didehydroshikimate. This latter compound tautomerizes to form the redox equivalent gallic acid, gallate dioxygenase is an enzyme found in Pseudomonas putida that catalyses the reaction gallate + O2 → -4-oxobut-1-ene-1,2, 4-tricarboxylate. Gallate decarboxylase is another enzyme in the degradation of gallic acid, gallate 1-beta-glucosyltransferase is an enzyme that uses UDP-glucose and gallate, whereas its two products are UDP and 1-galloyl-beta-D-glucose. It is a carbonic anhydrase inhibitor. In basic research, gallic acid extracted from seeds has been shown to inhibit the formation of amyloid fibrils, one of the potential causes of Alzheimers disease. One study indicated that gallic acid has this effect on amyloid protein formation by modifying the properties of alpha-synuclein, gallic acid is classified as a mutagen and a teratogen. Gallic acid is found in a number of plants, such as the parasitic plant Cynomorium coccineum, the aquatic plant Myriophyllum spicatum. Gallic acid is found in various oak species, Caesalpinia mimosoides

4.
Ellagic acid
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Ellagic acid is a natural phenol antioxidant found in numerous fruits and vegetables. The antiproliferative and antioxidant properties of ellagic acid have prompted research into its health benefits. Ellagic acid is the dilactone of hexahydroxydiphenic acid, plants produce ellagic acid from hydrolysis of tannins such as ellagitannin and geraniin. Urolithins are microflora human metabolites of dietary ellagic acid derivatives Ellagic acid was first discovered by chemist Henri Braconnot in 1831, maximilian Nierenstein prepared this substance from algarobilla, dividivi, oak bark, pomegranate, myrabolams, and valonea in 1905. He also suggested its formation from galloyl-glycine by Penicillium in 1915, löwe was the first person to synthesize ellagic acid by heating gallic acid with arsenic acid or silver oxide. Ellagic acid is found in species like the North American white oak. The macrophyte Myriophyllum spicatum produces ellagic acid, Ellagic acid can be found in the medicinal mushroom Phellinus linteus. The highest levels of acid are found in walnuts, pecans, cranberries, raspberries, strawberries. It is also found in peach, and other plant foods, Ellagic acid has antiproliferative and antioxidant properties in a number of in vitro and small-animal models. The antiproliferative properties of acid may be due to its ability to directly inhibit the DNA binding of certain carcinogens, including nitrosamines. As with other antioxidants, ellagic acid has a chemoprotective effect in cellular models by reducing oxidative stress. Ellagic acid has been marketed as a supplement with a range of claimed benefits against cancer, heart disease. Ellagic acid has been identified by the U. S. Food, urolithins, such as urolithin A, are microflora human metabolites of dietary ellagic acid derivatives that are under study as anti-cancer agents. Claims that ellagic acid can treat or prevent cancer in humans have not been proven, list of ineffective cancer treatments A Food-Based Approach to the Prevention of Gastrointestinal Tract Cancers - video lecture dedicated mainly to ellagic acid. Read by Dr. Gary D. Stoner from the Ohio State University Comprehensive Cancer Center, polyphenols as cancer chemopreventive agents, J. Cell Biochem Suppl

5.
Chemical formula
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These are limited to a single typographic line of symbols, which may include subscripts and superscripts. A chemical formula is not a name, and it contains no words. Although a chemical formula may imply certain simple chemical structures, it is not the same as a full chemical structural formula. Chemical formulas can fully specify the structure of only the simplest of molecules and chemical substances, the simplest types of chemical formulas are called empirical formulas, which use letters and numbers indicating the numerical proportions of atoms of each type. Molecular formulas indicate the numbers of each type of atom in a molecule. For example, the formula for glucose is CH2O, while its molecular formula is C6H12O6. This is possible if the relevant bonding is easy to show in one dimension, an example is the condensed molecular/chemical formula for ethanol, which is CH3-CH2-OH or CH3CH2OH. For reasons of structural complexity, there is no condensed chemical formula that specifies glucose, chemical formulas may be used in chemical equations to describe chemical reactions and other chemical transformations, such as the dissolving of ionic compounds into solution. A chemical formula identifies each constituent element by its chemical symbol, in empirical formulas, these proportions begin with a key element and then assign numbers of atoms of the other elements in the compound, as ratios to the key element. For molecular compounds, these numbers can all be expressed as whole numbers. For example, the formula of ethanol may be written C2H6O because the molecules of ethanol all contain two carbon atoms, six hydrogen atoms, and one oxygen atom. Some types of compounds, however, cannot be written with entirely whole-number empirical formulas. An example is boron carbide, whose formula of CBn is a variable non-whole number ratio with n ranging from over 4 to more than 6.5. When the chemical compound of the consists of simple molecules. These types of formulas are known as molecular formulas and condensed formulas. A molecular formula enumerates the number of atoms to reflect those in the molecule, so that the formula for glucose is C6H12O6 rather than the glucose empirical formula. However, except for very simple substances, molecular chemical formulas lack needed structural information, for simple molecules, a condensed formula is a type of chemical formula that may fully imply a correct structural formula. For example, ethanol may be represented by the chemical formula CH3CH2OH

6.
Gluconic acid
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Gluconic acid is an organic compound with molecular formula C6H12O7 and condensed structural formula HOCH24COOH. It is one of the 16 stereoisomers of 2,3,4,5, in aqueous solution at neutral pH, gluconic acid forms the gluconate ion. The salts of gluconic acid are known as gluconates, gluconic acid, gluconate salts, and gluconate esters occur widely in nature because such species arise from the oxidation of glucose. Some drugs are injected in the form of gluconates, the chemical structure of gluconic acid consists of a six-carbon chain with five hydroxyl groups terminating in a carboxylic acid group. In aqueous solution, gluconic acid exists in equilibrium with the cyclic ester glucono delta-lactone, gluconic acid occurs naturally in fruit, honey, and wine. As a food additive, it is an acidity regulator and it is also used in cleaning products, where it dissolves mineral deposits, especially in alkaline solution. The gluconate anion chelates Ca2+, Fe2+, Al3+, and other metals, in 1929 Horace Terhune Herrick developed a process for producing the salt by fermentation. Gluconate is also a present in certain solutions, such as plasmalyte a. Quinine gluconate is a salt between gluconic acid and quinine, which is used for injection in the treatment of malaria. Zinc gluconate injections are used to neuter male dogs, ferrous gluconate injections have been proposed in the past to treat anemia. Gluconic acid on NIST. gov ChemSub Online, D-Gluconic acid

7.
Casuarinin
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It is found in the pericarp of pomegranates. It is also found in Casuarina and Stachyurus species and in Alnus sieboldiana and it is an isomer of casuarictin. It is a highly active carbonic anhydrase inhibitor, in some plants including oak and chestnut, the ellagitannins are formed from 1,2,3,4, 6-pentagalloyl-glucose and further elaborated via oxidative dehydrogenation

8.
Pedunculagin
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It is formed from casuarictin via the loss of a gallate group. Pedunculagin is found in plants in orders in the clade Rosidae and it can be found the pericarp of pomegranates, in the family Lythraceae, in the order Myrtales. It is also found in the Indian gooseberry, a plant in the family Phyllanthaceae, galloyl pedunculagin can be found in Platycarya strobilacea. It is a highly active carbonic anhydrase inhibitor and it is an isomer of terflavin B